Methyl 4-aminobenzoate → 766556-60-9

HRID 1271710Notes

Reaction equation

HRID 1271710 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.Cl[CH2:13][CH2:14][CH2:15][N:16]=[C:17]=[O:18].[H-].[Na+]>C1COCC1>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([N:1]2[CH2:13][CH2:14][CH2:15][NH:16][C:17]2=[O:18])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 12082Methyl 4-aminobenzoateHCID 24758Sodium hydrideHCID 166752Propane, 1-chloro-3-isocyanato-

Product 1

HCID 69171359766556-60-9Yield 49.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Methyl 4-aminobenzoate (3.0 g, 20.0 mmol) and 1-chloro-3-isocyanato-propane (2.0 mL, 20.0 mmol) were stirred in THF (50 mL) at room temperature overnight. The solvents were evaporated. A THF (50 mL) solution of the residue (5.0 g, 18.51 mmol) was added to a stirred solution of NaH (60%, 0.93 g, 23.25 mmol) in THF (60 mL) portionwise at room temperature. The mixture was stirred for 3.5 h. It was evaporated. H2O was added. It was extracted with CH2Cl2, dried over MgSO4, filtered, and concentrated to dryness to give pure 4-(2-oxo-tetrahydro-pyrimidin-1-yl)-benzoic acid methyl ester as a white solid (2.15 g, yield: 49.6%). 1H NMR (DMSO-d6) δ 7.88 (d, J=8.5 Hz, 2H), 7.48 (d, J=8.6 Hz, 2H), 6.82 (s, br, 1H), 3.68 (m, 2H), 3.34 (s, 3H), 3.23 (m, 2H), 1.96 (m, 2H) ppm. LC-MS (ESI) 235.23 (M+H), tR=2.17 min (10–90% MeOH in H2O in a 4-min run).

Workup

  1. customThe solvents were evaporated
  2. customIt was evaporated
  3. additionH2O was added
  4. extractionIt was extracted with CH2Cl2
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9e3697af0cd949309c1779cf9a20e781
Source dataset
uspto-grants-2007_04
Patent number
US07205318B2

Reaction notes

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